Bisindolylmethane derivatives facilitate CuCl-catalyzed sonogashira cross-coupling reactions

Abstract

The invention discloses a method for promoting CuCl to catalyze Sonogashira cross-coupling reaction by a diindolylmethane derivative. According to the method, by taking the diindolylmethane derivative which are stable in water and air and are cheap and are easily available as a ligand, CuCl is promoted to catalyze Sonogashira cross-coupling reaction of aryl halide and terminal alkyne, so that not only is the use level of CuCl reduced, but also a conventional phosphine ligand needs not to be used. The method disclosed by the invention has good primer applicability, is suitable for aryl alkyne and alkyl terminal alkyne, and is high in yield of target products. The method is an efficient, low-consumption and safe Sonogashira cross-coupling reaction system which is wide in applicability and can be widely applied to constructing Csp-Csp2 bonds.

Description

technical field [0001] The invention belongs to the technical field of Sonogashira cross-coupling reaction, and in particular relates to a method for promoting CuCl-catalyzed Sonogashira cross-coupling reaction by bis-indolylmethane derivatives. Background technique [0002] The construction of carbon-carbon bonds plays a crucial role in the synthesis of bioactive molecules, drug molecules, and natural products. Among the currently existing carbon-carbon coupling reactions, the Sonogashira cross-coupling reaction synthesizes carbon-carbon bonds in a convenient way, and is favored by many scientific researchers. Among them, the Sonogashira cross-coupling reaction catalyzed by transition metals often uses noble metal Pd, and typical catalytic systems include the classic Pd / Cu bimetallic catalytic system with phosphine ligands and the single metal Pd catalytic system with phosphine ligands (K.Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 16, 4467–4470.). The...

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Problems solved by technology

However, these ligands usually produce pungent volatile gases. In some systems, not only the amount of ligands used is relatively large (20% to 30%), but also a large amount of copper salts (10% to 20%) are required, which is easy to cause environmental pollution. pollution, and such ligands are generally sensitive to oxygen and moisture, unstable in air, and most structures are difficult to modify and derivatize